Issue 3, 2016
From the journal:

Chemical Communications

Cyclopropenone-caged Sondheimer diyne (dibenzo[a,e]cyclooctadiyne): a photoactivatable linchpin for efficient SPAAC crosslinking†

Dewey A. Sutton,a   Seok-Ho Yu,b   Richard Steet ORCID logo b  and  Vladimir V. Popik*a  

* Corresponding authors

a Department of Chemistry, University of Georgia, Athens, USA
E-mail: vpopik@uga.edu

b Complex Carbohydrate Research Center, University of Georgia, Athens, USA

Abstract

The first fully conjugated bis-cyclopropenone (photo-DIBOD), a derivative of dibenzo[a,e][8]annulene, has been synthesized. 350–420 nm irradiation of this robust compound results in the efficient formation of dibenzo [a,e] cyclooctadiyne, an unstable, but useful SPAAC cross-linking reagent. Since photo-DIBO doesn't react with organic azides, this method allows for the spatiotemporal control of the ligation of two azide-tagged substrates.

Graphical abstract: Cyclopropenone-caged Sondheimer diyne (dibenzo[a,e]cyclooctadiyne): a photoactivatable linchpin for efficient SPAAC crosslinking

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Article information

DOI
https://doi.org/10.1039/C5CC08106H
Article type
Communication
Submitted
28 Sep 2015
Accepted
02 Nov 2015
First published
02 Nov 2015

Chem. Commun., 2016,52, 553-556

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Cyclopropenone-caged Sondheimer diyne (dibenzo[a,e]cyclooctadiyne): a photoactivatable linchpin for efficient SPAAC crosslinking

D. A. Sutton, S. Yu, R. Steet and V. V. Popik, Chem. Commun., 2016, 52, 553 DOI: 10.1039/C5CC08106H

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